1,2,3-Propanetricarboxylicacid supplier

Name
TRICARBALLYLIC ACID
EINECS 202-733-3
CAS No. 99-14-9
Article Data81
CAS DataBase
Density 1.574 g/cm³
Solubility 50 mg/mL, clear in water
Melting Point 156-161 °C(lit.)
Formula C₆H₈O₆
Boiling Point 266.4 °C at 760 mmHg
Molecular Weight 176.126
Flash Point 129.2 °C
Transport Information
Appearance off-white to light brown fine crystalline powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Tricarballylicacid (6CI);1,2,3-Tricarboxypropane;3-Carboxyglutaric acid;Carballylic acid;NSC 2347;b-Carboxyglutaric acid;
PSA 111.90000
LogP -0.36340

Synthetic route

: 600-17-9
vinyl glycolic acid

: 201230-82-2
carbon monoxide

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
With HeMaRaphos; water; toluene-4-sulfonic acid; palladium dichloride In tetrahydrofuran at 125℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction;	86%

: 59210-90-1
Dimethyl 2-dimethoxycarbonylmethyl-3-nitro-1,1-cyclopropanedicarboxylate

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
With hydrogenchloride for 10h; Heating;	70%
With hydrogenchloride for 10h; Product distribution; Mechanism; Heating;	70%

: 2922-42-1
(-)-3-dehydroshikimic acid

A: 99-50-3
3,4-Dihydroxybenzoic acid

B: 99-14-9
tricarallylic acid

C: 149-91-7
3,4,5-trihydroxybenzoic acid

D: 184105-29-1
dihydrogallic acid

E: 87-66-1
2-hydroxyresorcinol

Conditions

Conditions	Yield
With air; Na1.5H1.5PO4 at 40℃; for 50h; Rate constant; Mechanism; other oxidant, var. time;	A 12 % Spectr. B 14 % Spectr. C 13% D n/a E 3 % Spectr.

...Expand

: 67-56-1
methanol

: 617-54-9
citraconic acid dimethyl ester

: 151-50-8
potassium cyanide

A: 25306-99-4
dimethyl 2-(methoxymethyl)succinate

B: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
at 25℃; und Behandeln des Reaktionsprodukts mit HCl oder NaOH bei 25grad;

...Expand

: 67-56-1
methanol

: 617-54-9
citraconic acid dimethyl ester

: 151-50-8
potassium cyanide

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
at 25℃; beim Kochen des Reaktionsprodukts mit HCl oder NaOH;

...Expand

: 78-88-6
2,3-Dichloroprop-1-ene

: 64-17-5
ethanol

: 151-50-8
potassium cyanide

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
zerlegt das Prokukt mit alkoholischem Kali;

...Expand

: 78-88-6
2,3-Dichloroprop-1-ene

: 151-50-8
potassium cyanide

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
With ethanol Zerlegen des Reaktionsproduktes mit alkohol.Kalilauge;

: 99-67-2
2-allyl-4-pentenoic acid

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
With nitric acid

: 6127-93-1
3-chlorocrotonic acid ethyl ester

: 151-50-8
potassium cyanide

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
With ethanol Zerlegen des Reaktionsproduktes mit Kaliumhydroxyd;

: 499-12-7
1 propene 1,2,3 tricarboxylic acid

A: 110-15-6
succinic acid

B: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
With bacterium succinicum n.sp; phosphate-buffer

: 499-12-7
1 propene 1,2,3 tricarboxylic acid

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
durch Natriumamalgam;
Durch elektolitische Reduktion von halb mit Natron neutralisierter Aconitsaeure in der Kaelte unter Verwendung einer Quecksilberkathode;
With sodium amalgam bei der Reduktion der Aconitsaeure mit Natriumamalgam entstehende Loesung des Natriumsalzes nach starker Verduennung mit Bleizucker und zerlegt den Niederschlag durch Schwefelwasserstoff;

: 585-84-2
cis-aconitic acid

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
With water; platinum Hydrogenation;

: 4023-65-8
trans-acotinic acid

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
Hydrogenation;
With water; platinum Hydrogenation;

: 96-23-1
1,3-Dichloro-2-propanol

: 151-50-8
potassium cyanide

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
bei nachfolgenden Verseifung;

: 52163-78-7
propane-1,2,2,3-tetracarboxylic acid

A: 99-14-9
tricarallylic acid

B: 15719-64-9, 15719-76-3, 97762-63-5
methylammonium carbonate

Conditions

Conditions	Yield
at 151℃;

: 5247-13-2
1,1,1-Tricyan-propan

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
With potassium hydroxide; ethanol

: 149-91-7
3,4,5-trihydroxybenzoic acid

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
With hydrogenchloride; potassium chlorate at 90℃; extrahiert mit Aether,trennt aus dem Aetherabdampfungsrueckstand die auskrystallisierende Trichlorbrenztraubensaeure ab und kocht die verduennte Mutterlauge mit Zinn und Salzsaeure;

: 4717-55-9
cyclohex-4-ene-1,3-dicarboxylic acid

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
beim Ozonisieren und folgenden Behandeln mit Kaliumpermanganat-Loesung bei 0grad.;

: 98198-38-0
3,4-dioxo-cyclopentanecarboxylic acid

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
With potassium hydroxide; dihydrogen peroxide

: 84660-84-4
4-carboxy-2,6-dihydroxypyridine

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
With hydrogenchloride; tin

: 996-82-7, 34727-00-9, 73177-21-6
sodium diethylmalonate

: 623-91-6
diethyl Fumarate

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
dann Kochen den erhaltenen Propan-α.α.β.γ-tetracarbonsaeure-tetraaethylester mit maessig verduennter Salzsaeure;
dann Kochen den erhaltenen Propan-α.α.β.γ-tetracarbonsaeure-tetraaethylester mit konz.Kalilauge;

: 151-50-8
potassium cyanide

: 6127-92-0
E-Ethyl β-chlorocrotonate

A: 97-65-4
2-methylenesuccinic acid

B: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
und nachfolgender Verseifung mit Kali;

...Expand

: 151-50-8
potassium cyanide

: 6127-92-0
E-Ethyl β-chlorocrotonate

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
With ethanol Zerlegen des Reaktionsproduktes mit Kaliumhydroxyd;

: 14314-67-1
2-<2,2,2-Trinitro-ethyl>-bernsteinsaeure

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
(hydrolysis);

: 3,3-Bis--2-aethoxycarbonyl-glutarsaeure-diaethylester

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
With hydrogenchloride at 110 - 120℃; Heating;

: 7686-77-3
3-cyclopentene-1-carboxylic acid

: 99-14-9
tricarallylic acid

Conditions

Conditions	Yield
With sodium hydroxide; potassium permanganate

: 6324-87-4
(2,5-dioxo-pyrrolidin-3-yl)-acetic acid

: 7664-93-9
sulfuric acid

: 99-14-9
tricarallylic acid

: 872264-22-7
(3-cyano-5-imino-2-oxo-pyrrolidin-3-yl)-acetonitrile

: 7664-93-9
sulfuric acid

: 99-14-9
tricarallylic acid

: 7664-93-9
sulfuric acid

: 3-carbamoylmethyl-2-imino-5-oxo-pyrrolidine-3-carboxylic acid ethyl ester

: 99-14-9
tricarallylic acid

: 7664-93-9
sulfuric acid

: 3-carbamoylmethyl-2,5-dioxo-pyrrolidine-3-carboxylic acid ethyl ester

: 99-14-9
tricarallylic acid

: cadmium(II) perchlorate hexahydrate

: 99-14-9
tricarallylic acid

: 116117-86-3
4-((2-(pyridine-4-yl)propyl)pyridine)

: 7732-18-5
water

: [Cd(hydro(tricarballylate))(1,2-di(4-pyridyl)propane)(H2O)]n

Conditions

Conditions	Yield
at 80℃; for 72h; High pressure; Sealed tube;	91%

...Expand

: 99-14-9
tricarallylic acid

: 1765-40-8
(bromomethyl)pentafluorobenzene

: tris(2,3,4,5,6-pentafluorobenzyl)(1,2,3-propanetricarboxylate)

Conditions

Conditions	Yield
Stage #1: tricarallylic acid With caesium carbonate In N,N-dimethyl-formamide for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: (bromomethyl)pentafluorobenzene In N,N-dimethyl-formamide at 20℃; for 16h; Schlenk technique; Inert atmosphere;	90%

: 99-14-9
tricarallylic acid

: 4756-10-9
propane-1,2,3-tricarboxylic acid (1,2-anhydride)

Conditions

Conditions	Yield
With acetic anhydride 1.) 45 deg C, 1h 2.) glacial CH3COOH, 65 deg C, 1h;	87%
With acetic anhydride at 20℃;	77.8%
beim Destillieren unter vermindertem Druck;

: 99-14-9
tricarallylic acid

: 64508-63-0
2-fluorobenzoic anhydride

: 6a-(2-fluorophenyl)dihydrofuro[2,3-b]furan-2,5(3H,6aH)-dione

Conditions

Conditions	Yield
With pyridine In m-xylene at 140℃;	85%

: trans-2-methyl-cyclohexylamine

: 99-14-9
tricarallylic acid

: 1,2,3-propanetricarboxylic acid tris(trans-2-methylcyclohexylamide)

Conditions

Conditions	Yield
With pyridine; triphenyl phosphite In 1-methyl-pyrrolidin-2-one at 100℃; for 4h;	80%

: europium(III) nitrate pentahydrate

: 99-14-9
tricarallylic acid

: Eu(HOOCCH(CH2COO)2)(H2O)2*10H2O

Conditions

Conditions	Yield
In H2O Eu-compd. and carboxy-compd. in H2O refluxed for 8 h; concentrated, EtOH added, washed with EtOH, dried in vac. at 80°Cfor 2 h, elem. anal.;	80%

: 99-14-9
tricarallylic acid

: 93-97-0
benzoic acid anhydride

: 100953-23-9
6a-phenyldihydrofuro[2,3-b]furan-2,5(3H,6aH)-dione

Conditions

Conditions	Yield
With pyridine In m-xylene at 140℃;	78%
at 150 - 160℃;

: 4916-57-8
1,2-bis(4'-pyridyl)ethane

: cadmium(II) sulfate octahydrate

: 99-14-9
tricarallylic acid

: [Cd2(hydro(tricarballylate))2(1,2-di(4-pyridyl)ethane)2]n

Conditions

Conditions	Yield
In water at 80℃; for 72h; High pressure; Sealed tube;	78%

...Expand

: Ni(2+)*CO3(2-)*Ni(OH)2*H2O = NiCO3*Ni(OH)2*H2O

: 99-14-9
tricarallylic acid

: 7732-18-5
water

: Ni(HOOCCH(CH2COO)2)(H2O)2*10H2O

Conditions

Conditions	Yield
In H2O Ni-compd. and carboxy-compd. in H2O refluxed for 8 h; concentrated, EtOH added, washed with EtOH, dried in vac. at 80°Cfor 2 h, elem. anal.;	75%

...Expand

: 99-14-9
tricarallylic acid

: 6057-90-5
β-alanine hydrochloride

: 1401230-29-2
C15H23N3O9

Conditions

Conditions	Yield
With 4-methyl-morpholine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃;	75%
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	75%

: 57011-48-0
1,3-diazido 2-propanol

: 99-14-9
tricarallylic acid

: tris(1,3-diazidopropan-2-yl) propane-1,2,3-tricarboxylate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Green chemistry;	73%

: 99-14-9
tricarallylic acid

: 111-92-2
dibutylamine

: N,N,N',N',N",N"-hexabutyl-propane-1,2,3-tricarboxamide

Conditions

Conditions	Yield
Stage #1: tricarallylic acid With thionyl chloride In N,N-dimethyl-formamide at 90℃; for 2h; Stage #2: dibutylamine With triethylamine In dichloromethane; N,N-dimethyl-formamide for 120h;	72%
Stage #1: tricarallylic acid With thionyl chloride; N,N-dimethyl-formamide at 90℃; for 2h; Stage #2: dibutylamine With triethylamine In dichloromethane for 120h;	72%

: 99-14-9
tricarallylic acid

: 49619-43-4
2-chlorobenzoic anhydride

: 6a-(2-chlorophenyl)dihydrofuro[2,3-b]furan-2,5(3H,6aH)-dione

Conditions

Conditions	Yield
With pyridine In m-xylene at 140℃;	70%

: 99-14-9
tricarallylic acid

: 108-93-0
cyclohexanol

: 3-Cyclohexyloxycarbonyl-pentanedioic acid dicyclohexyl ester

Conditions

Conditions	Yield
With sulfuric acid In toluene at 190℃; for 24h;	68%

: 4916-57-8
1,2-bis(4'-pyridyl)ethane

: zinc hydroxide hydrate

: 99-14-9
tricarallylic acid

: 7732-18-5
water

: [Zn(tricarballylic acid-2H)(1,2-bis(4-pyridine)ethane)](n)*4nH2O

Conditions

Conditions	Yield
In ethanol; water wet Zn(OH)2 was suspn. in water, 0.5 M soln. of tricarballylic acid was added, a soln. of pyridine-compound in abs. ethanol was added dropwise, left overnight; elem. anal.;	68%

...Expand

: 99-14-9
tricarallylic acid

: 56666-54-7
3-fluorobenzoic acid anhydride

: 6a-(3-fluorophenyl)dihydrofuro[2,3-b]furan-2,5(3H,6aH)-dione

Conditions

Conditions	Yield
With pyridine In m-xylene at 140℃;	68%

: 99-14-9
tricarallylic acid

: 108-91-8
cyclohexylamine

: 1,2,3-propanetricarboxylic acid tris(cyclohexylamide)

Conditions

Conditions	Yield
tricresole borate In xylene for 3h; Product distribution / selectivity; Heating / reflux;	67.2%

: 553-26-4
4,4'-bipyridine

: zinc hydroxide hydrate

: 99-14-9
tricarallylic acid

: 7732-18-5
water

: [Zn(tricarballylic acid-2H)(4,4'-bipyridine)](n)*3nH2O

Conditions

Conditions	Yield
In ethanol; water wet Zn(OH)2 was suspn. in water, 0.5 M soln. of tricarballylic acid was added, a soln. of bipyridine in abs. ethanol was added dropwise, left overnight; elem. anal.;	67%

...Expand

: chromium chloride hexahydrate

: 99-14-9
tricarallylic acid

: 7732-18-5
water

: 1310-73-2
sodium hydroxide

: Cr(HOOCCH(CH2COO)2)(H2O)2*14H2O

Conditions

Conditions	Yield
In H2O Cr-compd. dissolved in H2O, 1 M NaOH added, centrifuged, washed with H2O, dispersed in H2O with carboxy-compd. under continuosly stirring, refluxed for 8 h; cooled, filtered, concentrated, EtOH added, dried at 80°C for 2 h, dried in vac., elem. anal.;	65%

...Expand

: 99-14-9
tricarallylic acid

: 7003-32-9
2-METHYLCYCLOHEXYLAMINE

: 1,2,3-propanetricarboxylic acid tris(2-methylcyclohexylamide)

Conditions

Conditions	Yield
tricresole borate In xylene for 3h; Product distribution / selectivity; Heating / reflux;	63%
Stage #1: tricarallylic acid With pyridine; diisopropyl-carbodiimide at 50℃; for 3h; Stage #2: 2-METHYLCYCLOHEXYLAMINE for 8h;	61%
Stage #1: tricarallylic acid With pyridine; diisopropyl-carbodiimide at 50℃; for 3h; Stage #2: 2-METHYLCYCLOHEXYLAMINE for 8h;	61%

: 66-71-7
1,10-Phenanthroline

: zinc hydroxide hydrate

: 99-14-9
tricarallylic acid

: 7732-18-5
water

: [Zn(tricarballylic acid-2H)(1,10-phenanthroline)(H2O)]2*4H2O

Conditions

Conditions	Yield
In ethanol; water wet Zn(OH)2 was suspn. in water, 0.5 M soln. of tricarballylic acid was added, a soln. of phenanthroline in abs. ethanol was added dropwise, left overnight; elem. anal.;	61%

...Expand

: 99-14-9
tricarallylic acid

: 790-41-0
4-chlorobenzoic anhydride

: 6a-(4-chlorophenyl)dihydrofuro[2,3-b]furan-2,5(3H,6aH)-dione

Conditions

Conditions	Yield
With pyridine In m-xylene at 140℃;	61%

: Gd(3+)*H(1+)*H2CCO2CHCO2CH2CO2(3-)=Gd(H2CCO2CHCO2CH2CO2H)(1+)

: 99-14-9
tricarallylic acid

: Gd(3+)*2H(1+)*2H2CCO2CHCO2CH2CO2(3-)=Gd(H2CCO2CHCO2CH2CO2H)2(1-)

Conditions

Conditions	Yield
In water byproducts: H(1+); reaction of Gd(tricarballylateH)(1+) with tricarballylic acid at pH 3.00; nuclear magnetic relaxation;	60%

: manganese(II) chloride monohydrate

: 99-14-9
tricarallylic acid

: [Mn3(tricarballylic acid-3H)2(H2O)4]n

Conditions

Conditions	Yield
With NaOH In water High Pressure; by a react. of Mn-contg. compd. (0.5 mmol), tricarballylic acid (0.25 mmol), NaOH (1 mmol) in aq. soln. in Teflon-lined autoclave; heating at 160°C for 120 h; cooling over a period of 12 h at a rate of 10°C/h; crystals were collected by filtration, washed with water, and dried at ambient temp.; elem. anal.;	59%

: 99-14-9
tricarallylic acid

: 25753-16-6
4-(trifluoromethyl)benzoic anhydride

: 6a-(4-(trifluoromethyl)phenyl)dihydrofuro[2,3-b]furan-2,5(3H,6aH)-dione

Conditions

Conditions	Yield
With pyridine In m-xylene at 140℃;	59%

: 99-14-9
tricarallylic acid

: 6-chlorohexanoic anhydride

: C11H15ClO4

Conditions

Conditions	Yield
With calcium chloride at 150℃; for 8h;	57%

: 99-14-9
tricarallylic acid

: 541-88-8
Chloroacetic anhydride

: 1361185-57-0
1-chloromethyl-2,8-dioxabicyclo[3.3.0]octane-3,7-dione

Conditions

Conditions	Yield
With dmap at 180℃; under 200 Torr; for 3h;	56%

: 99-14-9
tricarallylic acid

: 21436-44-2
3-methylbenzoic acid anhydride

: 6a-(m-tolyl)dihydrofuro[2,3-b]furan-2,5(3H,6aH)-dione

Conditions

Conditions	Yield
With pyridine In m-xylene at 140℃;	56%

1,2,3-Propanetricarboxylicacid Specification

The 1,2,3-Propanetricarboxylicacid, with the CAS registry number 99-14-9 and EINECS registry number 202-733-3, has the systematic name of propane-1,2,3-tricarboxylic acid. It is a kind of off-white to light brown fine crystalline powder, and the molecular formula of the chemical is C₆H₈O₆.

The characteristics of 1,2,3-Propanetricarboxylicacid are as followings: (1)ACD/LogP: -1.33; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4.3; (4)ACD/LogD (pH 7.4): -7.01; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 6; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 78.9 Å²; (13)Index of Refraction: 1.529; (14)Molar Refractivity: 34.49 cm³; (15)Molar Volume: 111.8 cm³; (16)Polarizability: 13.67×10^-24cm³; (17)Surface Tension: 79.2 dyne/cm; (18)Density: 1.574 g/cm³; (19)Flash Point: 129.2 °C; (20)Enthalpy of Vaporization: 55.52 kJ/mol; (21)Boiling Point: 266.4 °C at 760 mmHg; (22)Vapour Pressure: 0.00249 mmHg at 25°C.

Uses of 1,2,3-Propanetricarboxylicacid: It can react with cyclohexanol to produce 3-cyclohexyloxycarbonyl-pentanedioic acid dicyclohexyl ester. This reaction will need reagent sulfuric acid, and the menstruum toluene. The reaction time is 24 hours with temperature of 190°C, and the yield is about 68%.

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C(O)CC(C(=O)O)CC(=O)O
(2)InChI: InChI=1/C6H8O6/c7-4(8)1-3(6(11)12)2-5(9)10/h3H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
(3)InChIKey: KQTIIICEAUMSDG-UHFFFAOYAL

Product Name

TRICARBALLYLIC ACID

Synthetic route

1,2,3-Propanetricarboxylicacid Specification

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